Raymond's Trumpy wingman rolls in

Photo doctored to include the hat.

One of Portland city administrator Raymond Lee III's close henchpeople in his old gig in Greeley, Colorado – a guy who abruptly departed city government there, without explanation, at the same time Lee did – has surfaced in Oregon. Paul Trombino III, who was Lee's "managing director" in Greeley, has shown up in Albany, Oregon as the new public works director for that city. What a coincidence!

And with not one but two deputy administrator positions about to be officially opened up for "recruitment" in Portland – the headhunters who brought RL3 to town will be leading the "search" – I'd put the odds at better than even that Trombino will be a highly compensated honcho in Portland government before too long, or at least trying hard to become one.

So who is this fellow Trombino? Not your typical Portland bureaucrat type, that's for sure.

Most prominently, he was Donald Trump's first nominee to be head of the Federal Highway Administration, in 2017. His nomination made it through the appropriate Senate committee, but it was withdrawn before it made it to the Senate floor. Trombino said he withdrew because he needed to stay in Iowa with his sick father. There's no evidence publicly available anywhere to show that that was not the real story, but it was the kind of sequence that happens when a nominee gets "red carded" by somebody important in the Senate. 

By the time of his nomination, Trombino had spent 17 years in Wisconsin state government, five and a half years as the Iowa state transportation director, and a year running a private engineering company. After the aborted federal nomination, he did another year at the private firm, and then, whoa, he spent a couple of years as the chief operating officer of the entire executive branch of the State of Iowa under Republican Governor Kim Reynolds. 

In 2021, Reynolds appointed Trombino as Iowa Department of Homeland Security director. But he stayed in that job only 19 weeks before leaving to "pursue other opportunities." He made headines when he got to keep around $17,000 in retention bonus money despite his sudden departure.

The "other opportunities" were to work under Raymond Lee in Greeley, population 101,000, which Trombino did for about five years before last fall's abrupt housecleaning. He worked his way up from public works director to second or third in command in the Lee "cabinet." (The current Greeley city manager has dismantled the "cabinet" and reportedly saved more than a half-million dollars from the city manager's annual budget in the process.)

One other Trombino career entry is worth noting. In April of last year, he was a finalist for city manager in Palm Coast, Florida. But he pulled out of the running there, following the in-person look-see interviews, when it appeared to some that he might not get an offer. In the course of that candidacy, the same old headhunter firm rounded up hundreds of pages of media mentions of Trombino, here.

And so here we are. A few months after the departure of the motley entourage from Greeley, Trombino moves to Oregon, a mere 70 miles away from RL3. Neither guy seems to have had any previous contact with the area. Any rational person would suspect that PT3 has his sights set on a grand reunion with his old boss on the public pad here in the Rose City. You wonder what he told the folks in Albany about what brought him there.

There probably aren't going to be too many more career stops for Trombino. He appears to be pushing 60 years old, nearly 20 years older than Raymond. Once on the verge of being one of the most powerful transportation officials in the world, Trombino's currently running public works for a town of 58,000 people.

Would hiring him in Portland necessarily be a bad thing? To see Portland's bicycle toy programs and water filtration boondoggle being overseen by a former Trump lieutenant would be uniquely entertaining. But as Lee's appointment illustrates, the concept of absurdity has become obsolete under the new city charter. The crazier something sounds, the more likely it is to happen.

Maybe Trombino will be portrayed by the headhunters, off the record, as the brains of the operation – a way to cope with the liabilities that Portland assumed when it hired Lee. A mere $275,000-plus-perks to salvage the initial $375,000-plus-perks.

Anyway, we wait with anticipation for the next shoe to drop. Nobody in Portland City Hall bothered to dig into what happened in Greeley that triggered Lee's departure. Will they double down with Trombino without further investigation? I wish I could say no. 

Maybe his MAGA background will give Mayor Keith Wilson some pause. Maybe.